(6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one

Base Information

• Chemical Name: (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one
• CAS No.: 881667-65-8
• Molecular Formula: C₂₆H₃₀O₆
• Molecular Weight: 438.521
• Mol file: 881667-65-8.mol

Synonyms:(6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one

Chemical Property of (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one

There total 6 articles about (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

2-((2S,4S)-6-Benzyloxy-2-benzyloxymethoxy-4-hydroxy-hexyl)-pyran-4-one (881667-64-7) → (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one (881667-65-8)

Guidance literature:

With trifluoroacetic acid; In benzene; at 20 ℃; for 72h;

DOI:10.1021/ol0601601

Reference yield:

6-[(2S,4S)-6-Benzyloxy-2-hydroxy-4-(4-methoxy-benzyloxy)-hexyl]-2,2-dimethyl-[1,3]dioxin-4-one (881667-67-0) → (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one (881667-65-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / N,N-diisopropylethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Heating

2: toluene / 3.5 h / 110 °C

3: 1.24 g / p-toluenesulfonic acid / tetrahydrofuran / 2 h / Heating

4: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; buffer / CH₂Cl₂ / 1 h / pH 7

5: 64 percent / trifluoroacetic acid / benzene / 72 h / 20 °C

With dmap; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; benzene; 2: Diels-Alder reaction;

DOI:10.1021/ol0601601

Reference yield:

2-[(2S,4S)-6-Benzyloxy-2-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-hexyl]-pyran-4-one (881667-63-6) → (6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-1,7-dioxa-spiro[5.5]undec-2-en-4-one (881667-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; buffer / CH₂Cl₂ / 1 h / pH 7

2: 64 percent / trifluoroacetic acid / benzene / 72 h / 20 °C

With trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene;

DOI:10.1021/ol0601601

upstream raw materials:

2-((2S,4S)-6-Benzyloxy-2-benzyloxymethoxy-4-hydroxy-hexyl)-pyran-4-one

6-[(2S,4S)-6-Benzyloxy-2-hydroxy-4-(4-methoxy-benzyloxy)-hexyl]-2,2-dimethyl-[1,3]dioxin-4-one

2-[(2S,4S)-6-Benzyloxy-2-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-hexyl]-pyran-4-one

6-[(2S,4S)-6-Benzyloxy-2-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-hexyl]-2,2-dimethyl-[1,3]dioxin-4-one

Downstream raw materials:

(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-2-vinyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol

(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-benzyloxymethoxy-4-methyl-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol